Functional fluid containing a sludge inhibiting detergent comprising the polyamine salt of the reaction product of maleic anhydride and an oxidized interpolymer of propylene and ethylene



United States Patent Ofiice 3,3 l hi 7? Patented Apr. 25, 1967 3,316,177FUNCTIUNAL FLUID CONTAINING A SLUDGE of Ohio No Drawing. Filed Dec. 7,1964, Ser. No. 416,618

9 Claims. (Cl. 25251.5)

This invention relates to a novel composition of matter. In a moreparticular sense it relates to a nitrogen-containing composition whichis useful as an additive in fuels, lubricants, petroleum fractions, etc.The nitrogencontaining composition of this invention is especiallyeffective as an additive to inhibit the formation of harmful deposits inhydrocarbon compositions such as petroleum refinery fractions.

Most of the gasoline produced today is obtained by the thermal orcatalytic cracking of heavier petroleum hydrocarbon feed stocks such aslight or heavy gas oils, cycle stocks, virgin or topped crude oils, lubestocks, kerosene, and kerosene-gas oil mixtures. A number of differentthermal and/or catalytic cracking processes known in the petroleumindustry under designations such as Fluid Process, Thermofor, Houdry,Platforming, Thermal Reforming, Viscosity-Breaking, etc., are employedfor the purpose. Although these various processes differ considerably asto the precise manner in which the heavier hydorcarbon molecules arecracked to yield gasoline, they all involve the heating of thehydrocarbon feed stock to a high temperature (370-1200- F.) and thepassage of such heated stock, optionally mixed with a cracking catalyst,through heated tubes, reactors, convertors, and tower stills.

Regardless of the particular process used, the cracking operation alwaysresults in the formation of some undesirable carbonaceous material orrefinery coke which adheres to the tubes, reactors, etc., of thecracking unit and lowers its efliciency, principally by impeding theflow of the feed stock therethrough and the transfer of heat to or fromsuch stock. After enough carbonaceuos material has accumulated on thevarious parts of the cracking unit to lower its efficiencysubstantially, the unit must be dismantled, cleaned, and reassembled. Ofcourse, such cleaning operations are not only tedious and costly, butresult in a large proportion of down-time during which the unit is notfunctioning. Although the use of modern Platforming and catalyticcreacking processes has reduced the amount of down-time as compared witholder, strictly thermal cracking processes, the accumulation of refinerycoke still presents a problem to the petroleum refining industry.

It is accordingly a principal object of this invention to provide novelcompositions of matter.

object of this invention to provide addit1ves in fuels, lubricants,petroleum fractions and other hydrocarbon compositions.

It is another object of this invention to provide improved fuels,lubricants and hydrocarbon compositions.

It is another object of this invention to inhibit the formation ofharmful deposits in refinery cracking units.

It is another object of this invention to inhibit the accumulation ofharmful deposits in hydrocarbon compositions which are subjected to hightemperature and pres sure.

It is another object of this invention to inhibit the formation ofharmful deposits in heat exchange units.

These and other objects are attained in accordance Cleveland, Ohio,assignor to The with this invention 'by providing a nitrogen-containingcomposition prepared by the process comprising reacting an oxidized,degraded interpolymer of propylene and ethylene having a molecularweight of at least about 1000 with from about 1% to about 20% by weightof maleic anhydride to form an acidic intermediate and neutralizing saidacidic intermediate with an alkylene polyamine.

The acidic composition, described above as the acidic intermediate, isuseful as an intermediate for preparing other compositions, e.g., metalsalts including those of zinc and barium, which are likewise useful asimprovement agents for lubricating compositions.

The oxidized, degraded interpolymers useful in the above process arederived principally from ethylene and propylene. They may include minoramounts, i.e., up to about 10% based on the molar amounts of monomericethylene and propylene units in the interpolymer, of polymerized unitsderived from other monomers. EX- amples of such other monomers includepolymeriza'ble monolefins having at least 4 carbon atoms such aslbutene, l-pentene, Z-butene, 3-hexene, 4-methyl-11pentene, l-decene,l-nonene, 2-methyl-propene and l-dodecene. They include also polyenes,i.e., those having 2 or more olefinic linkages, such as conjugatedpolyenes, for example, butadiene, isoprene, piperylene, 1,3-hexadiene,1,3-octadiene, 2,4-decadiene, etc, They may further be non-conjugatedpolymers such as 3,3-dirnethyl- 1,5-hexadiene, 1,9-decadiene,di-cyclopentadiene, 1,19- eicosadiene, 1,4-pentadiene, 1,5-hexadiene,etc. The latter non-conjugated dienes are especially useful in theinterpolymer. For the most part, such other monomers preferably containfrom 4 to about 10 carbon atoms although they may contain as many as 25carbon atoms.

The interpolymers containing from about 20% to about (molar) ofpolymerized propylene, from about 30% to about of polymerized ethylene,and up to about 10% of another polymerized olefin are useful and thosecontaining from about 25% to about 50% of polymerized propylene, fromabout 50% to about 75 of polymerized ethylene and from about 1% to about10% of a polymerized non-conjugated diene are preferred.

The interpolymers from which the oxidized, degraded interpolymers of theabove process are derived usually have molecular weights of at leastabout 50,000. They may have molecular weights of as high as 800,000 orhigher. The interpolymers having molecular weights ranging from about80,000 to about 600,000 are especially useful.

The oxidized, degraded interpolymers of this invention are prepared mostconveniently by heating an interpolymer illustrated above at atemperature of at least about C. in the presence of oxygen or air so asto cause the degradation of the interpolymer. Such degradation isusually characterized by a. substantial reduction of the molecularweight of the interpolymer. The mechanism by which the interpolymer isdegraded is not precisely known; nor is the chemical composition of theoxidized, degraded product. It is known, however, that 'an oxidized,degraded interpolymer having a molecular weight of at least about 1000is useful in the process of this invention and so also is one which hasbeen oxidized and degraded to the extent that its molecular weight is atleast about 5% less than the molecular weight of the interpolymer beforedegradation. The oxidized, degraded interpolymer having a molecularweight of from about 3000 to about 5000 or as high as about 200,000 ispreferred for use in the process of this invention.

A particularly useful method of preparing the oxidized and degradedinterpolymer involves heating a fluid solution of a suitableinterpolymer in an inert solvent and J2 )ubbling oxygen or air throughthe solution at a tempera- :ure of at least about 100 C. until thedesired degradation is achieved. In lieu of oxygen or air, any mixtureof oxygen and inert gas such as nitrogen or carbon dioxide may be used.The inert gas thus functions as a carrier of oxygen and often provides aconvenient means if introducing oxygen into the reaction mixture.

The inert solvent useful in preparing the fluid solution of theinterpolymer reactant is preferably a liquid inert hydrocarbon such asnaphtha, hexene, cyclohexane, dodecane, biphenyl, xylene or toluene. Itmay be a polar solvent such as diphenyl oxide. The amount of the solventto be used is not critical so long as .a sufficient amount is used toresult in the fluid solution of the interpolymer. Such solution usuallycontains from about 60 to 95% of a solvent.

The temperature at which the interpolymer is oxidized and degraded is atleast about 100 0, preferably at least about 150 C. and it may be ashigh as 250 C., 300 C. or even higher.

The alkylene polyamine useful in the process of this invention conformsfor the most part to the structural formula:

H N alkylene-NH H wherein x has a value from 1 to about 12 and thealkylene radical may contain from 2 to about 12 carbon atoms and ispreferably a lower alkylene radical, i.e., one having up to about 6carbon atoms. Thus the alkylene polyamine may be ethylene diamine,diethylene, triamine, triethylene tetramine, tetraethylene pentamine,trimethylene diamine, N,N-dimethyl(trimethylenediamine),bis(dimethy1aminopropyl)amine, propylene diamine, tetramethylenediamine, tbutylene diamine, N-aminoethyl trimethylene diamine, N-dodecylpropylene diamine, di-(trimethylene) triamine, pentaethylene hexamine,etc. It includes also higher and cyclic homologues of such amines suchas piperazines. The ethylene polyamines are especially useful. They arediscussed in some detail under the heading Ethylene Amines inEncyclopedia of Chemical Technology Kirk and Othmer, volume 5, pages898-805, Interscience Publishers, New York (1950). Such compounds areprepared most conveniently by the reaction of an alkylene dihalide,e.g., ethylene dichloride, with ammonia or a primary amine. Thisreaction results in the production of somewhat complex mixtures ofalkylene polyamines including cyclic condensation products such aspiperazine, N-aminoethyl-piperazine, etc. These mixtures find use in theprocess of this invention. On the other hand, quite satisfactoryproducts may be obtained also by the use of pure alkylene amines. Anespecially useful alkylene polyamine for reasons of economy as well aseffectiveness of the products derived therefrom is a mixture of ethylenepolyaniines prepared by the reaction of ethylene chloride and ammoniaand having an average of from 2 to 7 amino groups per molecule.

The process by which the nitrogen-containing composition of thisinvention is prepared usually involves heating the oxidized, degradedinterpolymer with from about 1% to about 20%, preferably from 2% toabout 10% (by weight), of maleic anhydride at a temperature of at leastabout 80 0., preferably from about 100 C. to 250 C., to form an acidicintermediate and then neutralizing the acidic intermediate :by mixing itwith the alkylene polyamine reactant at a temperature of at least about25 0, preferably from about 80 C. to about 250 C. A higher temperaturemay be used in the process provided that it does not exceed thedecomposition point of the reaction mixture.

The process may be carried out in the presence of a solvent such asxylene, benzene, naphtha, chlorobenzene, nitrobenzene, or diphenylether. Mineral oil is especially useful as the solvent. The use of asolvent is particularly advantageous in cases where one of the reactantsis a viscous liquid or a solid; the solvent in such cases functions tofacilitate the mixing of the reactants and the control of the reactiontemperature.

The chemical composition of the acidic intermediate or the product,i.e., the nitrogen-containing composition, of the above process is notfully understood. The acidic intermediate is believed to be either asubstituted maleic anhydride or a substiuted succinic anhydride or amixture thereof. The manner in which the anhydride radical is combinedwith the interpolymer portion of the molecule is not known; nor is itknown whether one or more anhydride radicals are combined with aparticular interpolymer chain. It is known, however, that the reactionproduct of the interpolymer and maleic anhydride is acidic and isneutralized by the alkylene amine reactant in the above process to formthe desired product. In this regard it is noted that the amount of thealkylene polyamine reactant to be used in the process depends to a largeextent on the acidity of the acidic intermediate, that is, the amount ofthe alkylene polyamine reactant to be used in the process is chemicallyequivalent to the acidic intermediate. However, from about 0.8equivalent to about 2 or more equivalents of the alkylene polyamine perequivalent of the acidic intermediate may be used. The equivalent weightof an amine depends on the number of amino groups in a molecule. has 3equivalents per mole.

The chemical composition of the product, i.e., the nitrogen-containingcomposition, of the above process is not fully understood. It depends tosome extent upon the temperature at which the product is formed. Forinstance, where the reaction of the acidic intermediate and the alkyleneamine is carried out at a temperature below about C., the product willcontain a substantial quantity of an amine salt whereas if such reactionis carried out at a temperature above about C., the product will containa substantial quantity of an imide, amide or amidine. In .mostinstances, the product will be a complex mixture, the precisecomposition of which is not known. It is known, however, that theproduct, regardless of the relative proportions of its components, isuseful for the purposes of this invention.

The following examples illustrate the preparation of thenitrogen-containing compositions of this invention.

Example 1 Tetrachloroethylene (31.) is passed through a silica gelcolumn, sparged with nitrogen and then added under nitrogen to a dryreaction flask at 25 C. Agitation is begun and an equirnolar mixture ofgaseous ethylene and propylene is introduced below thetetrachloroethylene liquid surface at a rate of .100 ml. per seconduntil a saturated monomer solution is obtained, the excess of gas beingallowed to escape through a gas outlet tube. To this saturated monomersolution there is added 8 ml. (0.0128 mole) of a 1.6 molar solution ofaluminum triisobutyl in cyclohexane and 0.94 ml. (0.010 mole) of vanadyltrichloride, separately and rapidly in turn, by means of syringes,through an opening in the reactor sealed with a soft rubber cap. Thetetrachloroethylene solution turns to a clear amber color and thetemperature rises to about 40 C. after a minute. To the agitatedreaction mixture at 35 40 C., an equimolar mixture of gaseous ethyleneand propylene is introduced at a rate of 100 ml. per second over aperiod of 0.5 hours. To the reaction mixture there is added 5 ml. ofn-butanol and the polymer separates as a rubbery swollen solid which issqueezed free of excess solvent, washed several times with freshn-butanol, and dried. The copolymer thereby obtained has a propylenecontent of 20 mole percent and a molecular weight of 250,000. Thiscopolymer is then dissolved in four times its weight of diphenyl oxideand blown with oxygen at a temperature of 150180 C. for 6 hours. Theoxidized, degraded polymer is found to have a molecular weight of 5000.A portion of the oxidized, degraded polymer in diphenyl oxide is mixedwith For instance, diethylene triarnine 1% (by weight of the polymer) ofmaleic anhydride and the mixture is heated at 200 C. for 3 hours to forman acidic product. The acidic product is then neutralized with astoichiometric amounts of ethylene diamine at 120150 C. The reactionmixture is dissolved in SAE 20 mineral oil and is heated at 120-l50 C./1mm. to distill off volatile components. The residue is an oil solutionof the nitrogen-containing product.

Example 2 A solution of 30 grams (0.15 mole) of aluminum triisobutyl and84 grams (0.6 mole) of decene-l in 200 ml. of tetrachloroethylene washeated at reflux under a nitrogen atmosphere for 2 hours to formaluminum tridecyl. The solution was cooled to room temperature andblended with 1800 ml. of tetrachloroethylene, presaturated with anethylene-propylene gas mixture containing 75 mole percent of propylene.The ethylenepropylene gas mixture (75 mole percent propylene) is fedinto the tetrachloroethylene solution at a rate 37.5 ml. per second.Introduction of ethylene and propylene is continued as a solution of4.35 grams (0.025 mole) of ml. of tetrachloroethylene is added to thereaction mixture with vigorous stirring at 29 -41 C. over a period of 2minutes. The catalyst forms a clear violet solution and rapid absorptionof the gas feed commences. Thereafter, 30 ml. (0.108 mole) of a 3.6molar solution of 1,4-hexadiene in tetrachloroethylene is added over aperiod of 9 minutes to the reaction mixture at 41-48 C. The feed ofethylene and propylene is continued and 53.4 ml. (0.192 mole) more ofthe 3.6 molar, 1,4-hexadiene solution is added to the reaction mixtureover a period of 2 hours at 3840 C. Then, 6 l. of n-butanol are added tothe reaction mixture causing precipitation of an interpolymer. Theprecipitate is slurried with acetone in a Waring Blendor and then driedon a rubber mill at 50 C. The produce (97 grams) is a soft, rubberyterpolymer which has a propylene content of 42 mole percent, a dienecontent of 1.2 mole per- The terpolymer has an RSV of about 2.1,corresponding to a molecular weight of 125,500 (RSV is an abbreviationof reduced specific viscosity which means the specific viscosity,corrected to shear gradient divided by the concentration of the polymersolution in grams per 100 ml. In actual measurement, the viscosity isthat of a decalin solution, at 135 C., of the polymer at a concentrationof 0.1 gram in 100 ml. of the solution. The molecular weight of thepolymer is calculated according to the equation l'.SV=AM where M is themolecular weight, A and x are specific constants characteristic of thepolymer, Kirk and Othmer, Encyclopedia of Chemical Technology, (2ndSupp. 1960 at 663) and Gaylord and Mark, Linear and Stearyl RegularAddition Polymers, page 79 (1959). A soultion of 500 grams of thisinterpolynier in 2000 grams of diphenyl oxide is blown with oxygen at200225 C. for 4 hours. oxidized, degraded polymer solution (1830 grams)is mixed with maleic anhydride (41 grams) at 230 C. for 4 hours and thenheated at 200 C./1 mm. to remove volatile components. The residue, 383grams, is mixed with 383 grams of xylene and the xylene solution has anacid number of 22. A portion of this solution (100 grams) in 100 gramsof mineral oil is neutralized with twice the stoichiometric amount ofN,N-dimethyl trimethylenediamine at 90-170 C. whereupon water formedduring the reaction is distilled off. The residue is heated to 170 C./45mm. and filtered. The filtrate is a 65.3% oil solution of thenitrogen-containing product having a nitrogen content of 0.5.)

Example 3 A product is obtained by a procedure essentially the same asthat of Example 2 from these reactants: the oxidized, degradedinterpolymer of Example 2, maleic anhydride (10% by weight of thepolymer), a mixture of N,N-dimethyl trimethylenediamine and a commercialpolyethylene polyamine mixture having an average of 5 amino groups permolecule in a weight ratio of 9:1 (twice the stoichiometric amount. ofthe polymermaleic anhydride reaction product). The product is dissolvedin mineral oil and a 65% oil solution of the product has a nitrogencontent of 0.55%.

Example 4 dized, degraded interpolyrner of Example 2, maleic anhydride(5% by weight of the polymer), and N,N-di methyl trimethylenediamine(twice the equivalent amount of the polymer-maleic anhydride reactionproduct). The product is dissolved in mineral oil and a 66% oil solutionof the product has a nitrogen content of 0.37%.

Example 5 (2% by weight of the polymer), andbis-(dimethylaminopropyl)amine (twice the stoichiometric amount of thepolymer-maleic anhydride reaction product). The product is dissolved inmineral oil and a 62% oil solution of the product has a nitrogen contentof 1.27%.

Example 6 hydride (4.4% by weight of the polymer), and a commercialpolyethylene polyamine mixture having an average of 5 amino groups permolecule (1 equivalent per equivalent of the polymer-maleic anhydridereaction product).

The nitrogen-containing products of this invention are useful asadditives in fuels, lubricant compositions and hydrocarbon oils. Theyare effective to impart sludge inhibiting properties and detergentproperties to such compositions. They are especially useful as anadditive in refinery streams which are subjected to high temperaturecracking, distillation, reforming or similar operations.

cumulation of carbonaceous material which tend to be produced at hightemperatures. Thus, the nitrogen-containing products of this inventionhave found particular animal, vegetable, lubricating oils are preferredof their availability, general excellence, and low cost. For certainapplications, oils belonging to one of the other hree groups may bepreferred. The concentration of the .itrogen-containing products of thisinvention in a lubrizating composition may range from about 0.1% toabout more often from about 0.5% to by weight.

The liquid hydrocarbon fuels in which the nitrogen- :ontainingcompositions of this invention are useful in- :lude gasoline, dieselfuels and other distillate or residual JllIIlCl" fuel oils which arederived from petroleum by such nethods as distillation, thermal crackingor catalytic cracking. For the most part the burner fuel oil and dieselfuel have a minimum flash point of 80 F, maximum pour point of 70 F.,maximum point of 650 F, maximum 90% point of 900 F., minimum API gravityof 24 and a maximum viscosity value of 130 Saybolt Universal Seconds at100 F. The concentration of the nitrogen-containin g products of thisinvention in such fuels may range from about 0.0001% to about 5% moreoften from 0.001% to about 2%, by weight.

A unique characteristic of the nitrogen-containing compositions of thisinvention is their effectiveness under high temperature conditions suchas 300-1200 F. to impart sludge inhibiting and detergent properties tofuels, lubricants, oils and petroleum fractions. This effectiveness isdirectly related to the oxidized, degraded interpolymer from which thecompositions are derived. The manner in which such interpolymer impartsthe high temperature effectiveness to the compositions of this inventionis not fully understood. it is believed, however, that the oxidation anddegradation of the interpolymer results in a polymeric product which ishighly resistant to further oxidative and thermal degradation and thatsuch resistance is imparted to the nitrogen-containing compositions ofthis invention. A critical element of the present invention, therefore,is the use of the oxidized, degraded interpolymer in the process forpreparing the nitrogencontaining compositions which are useful for theherein described purposes.

The effectiveness of the nitrogen-containing products of this inventionas additives in lubricating compositions is shown by the results of anOxidation-Dispersancy test. In this test a 350 cc. sample of a lubricantcontaining the additive to be tested is heated at 300 F. for 144 hoursin a 2" x borosilicate tube. The lubricant base employed in the test isa Mid-Continent conventionally refined mineral oil having a viscosity ofabout 200 Saybolt Universal Seconds at 100 F. Air is bubbled through thelubricant at a rate of 10 l. per hour. The oxidized sample is allowed tocool to 122 F. and to stand for 15 hours at room temperature and thenfiltered through No. 1 Whatman paper (double thickness) under slightlyreduced pressure. The sludge deposit formed during the test is collectedon the filter paper, washed with naphtha to a constant weight andreported as milligrams of sludge per 100 cc. of oil. The smaller theamount of the sludge deposit the more effective the detergent additive.The results are shown in Table I below:

TABLE I.OXIDATION-DETERGENCY TEST Additive Tested (1.5% by weight of theof sludge/100 m1. of sample D 0:: Product oi Example 4...

The effectiveness of the nitrogen-containing products of this inventionas an additive in fuel oils is shown by the results (Table 11) of theFuel Oil Detergcncy test. In this test, a mixture of 4 l. of acatalytically cracked No. 2 light fuel oil and 15 grams of a syntheticsludge (prepared by homogenizing a 50/40/10, by weight, mixture ofdistilled Water/No. 2 uninhibited fuel oil/ carbon black) is circulatedfor 2 hours in a fuel oil burner pump equipped with a 100-mesh Monelstrainer. The sludge retained on the strainer is washed with acetone andweighed.

(7 r.) of the additive is indicated by the perthe sludge retained on thestrainer as compared to the sludge formed from the fuel oil containingno additive. A fuel whose rating is greater than 5 90% is considered tohave excellent anti-clogging properties.

TABLE II.FUEL OIL DETERGENCY TEST The effectiveness cent reduction ofTest Results Milligrams of Sludge Additive Tested (0.005% by f 10 weightin the test sample) With Without Percent Additive Additive ReductionProduct of Example 2 111.7 689 83. 8 Product of Example 4 108. 6 746 85.4

What is claimed is:

1. A petroleum fraction containing a minor amount, sufficient to impartsludge-inhibiting and detergent properties to said petroleum fraction,of a nitrogen-containing composition prepared by the process comprisingreacting an oxidized, degraded interpolymer of propylene and ethylene,said oxidized, degraded interpolymer having a molecular weight of tainedby heating said interpolymer at a temperature of at least about 100 C.in the presence of oxygen to cause a substantial reduction in themolecular weight of said interpolyrner, with from about 1% to about byweight of maleic anhydride to form an acidic intermediate andneutralizing said acidic intermediate with an alkylene polyamine.

2. A petroleum fraction containing a minor amount, sufficient to impartsludge-inhibiting and detergent properties to said petroleum fraction,of a nitrogen-containing composition prepared by the process whichcomprises reacting an oxidized, degraded interpolymer of propylene,ethylene, and a non-conjugated diene having from 4 to about 10 carbonatoms in proportions of from about 20 to about 70 mole percent ofpropylene, from about 30 to about 80 mole percent of ethylene, and fromabout 1 to about 10 mole percent of the diene, said oxidized, degradedinterpolymer having a molecular weight of from about 1000 to about 5000and being obtained by heating said interpolymer at a temperature of atleast about 100 C. in the presence of oxygen to cause a substantialreduction in the molecular weight of said interpolymer, 'with from about1% to about 20% by weight of maleic anhydride to form an acidicintermediate and neutralizing said acidic intermediate with from about 1to about 2 equivalents of an alkylene polyamine having from 2 to about 7amino groups.

3. The petroleum fraction of claim 2 wherein the alkylene polyamine is apolypropylene polyamine.

4. A hydrocarbon oil containing a minor amount, sulficient to impartsludge-inhibiting and detergent properties thereto, of a nitrogencontaining composition prepared by the process comprising reacting anoxidized, degraded interpolymer of propylene and ethylene, saidoxidized, degraded interpolymer having a molecular weight of at leastabout 1000 and being obtained by heating said interpolymer at atemperature of at least about 100 C. in the presence of oxygen to causea substantial reduction in the molecular weight of said interpolymer,with from about 1% to about 20% by weight of maleic anhydride to form anacidic intermediate and neutralizing said acidic intermediate with analkylene polyamine.

5. A hydrocarbon oil containing a minor amount, sufficient to impartsludge-inhibiting and detergent properties thereto, of anitrogen-containing com-position prepared by the process which comprisesreacting an oxidized, degraded interpolymer of propylene, ethylene, anda nonconjugated diene having from 4 to about 10 carbon atoms inproportions of from about 20 to about 70 mole percent of propylene, fromabout 30 to about 80 mole percent of ethylene, and from about 1 to about10 mole percent of the diene, said oxidized, degraded interpolymerhaving a at least about 1000 and being obmolecular weight of from about1000 to about 5000 and being obtained by heating said interpolymer at atemperature of at least about 100 C. in the presence of oxygen to causea substantial reduction in the molecular weight of said interpolymer,with from about 1% to about 20% by weight of maleic anhydride to form anacidic intermediate and neutralizing said acidic intermediate with fromabout 1 to about 2 equivalents of an alkylene polyamine having from 2 toabout 7 amino groups.

6. A lubricating composition comprising a major proportion of alubricating oil and a minor proportion, sulficient to impartsludge-inhibiting and detergent properties thereto, of anitrogen-containing composition prepared by the process comprisingreacting an oxidized, degraded interpolymer of propylene and ethylene,said oxidized, degraded interpolymer having a molecular weight of atleast about 1000 and being obtained by heating said interpolymer at atemperature of at least about 100 C. in the presence of oxygen to causea substantial reduction in the molecular weight of said interpolymer,with from about 1% to about 20% by weight of maleic anhydride to form anacidic intermediate and neutralizing said acidic intermediate With analkylene polyamine.

7. A lubricating composition comprising a major proportion of alubricating oil and a minor proportion, sufiicient to impartsludge-inhibiting and detergent properties thereto, of anitrogen-containing composition prepared by the process which comprisesreacting an oxidized, degraded interpolymer of propylene, ethylene, anda nonconjugated dicne having from 4 to about 10 carbon atoms inproportions of from about to about 70 mole percent ture of at leastabout 100 C. in the presence of oxygen to cause a substantial reductionin the molecular weight of said interpolymer, with from about 1% toabout 20% by Weight of maleic anhydride to form an acidic intermediateand neutralizing said acidic intermediate with from about 1 to about 2equivalents of an alkylene polyamine having from 2 to about 7 aminogroups.

8. A liquid hydrocarbon fuel containing a minor amount, sufiicient toimpart sludge-inhibiting and detergent properties thereto, of a nitrogencontaining composition prepared by the process comprising reacting anoxidized, degraded interpolymer of propylene and ethylene, saidoxidized, degraded inter-polymer having a molecular Weight of at leastabout 1000 and being obtained by heat ing said inter-polymer at atemperature of at least about 100 C. in the presence of oxygen to causea substantial reduction in the molecular weight of said interpolymer,With from about 1% to about 20% by Weight of maleic anhydride to form anacidic intermediate and neutralizing said acidic intermediate with analkylene polyamine.

9. A liquid hydrocarbon fuel containing a minor amount, sufficient toimpart sludge-inhibiting and detergent properties thereto, of anitrogen-containing composition prepared by the process which comprisesreacting an oxidized, degraded interpolymer of propylene, ethylene, anda non-conjugated diene having from 4 to about 10 carbon atoms inproportions of from about 20 to about 5000 and being obtained by heatingsaid interpolymer at a temperature of at least about C. in the presenceof oxygen to cause a substantial reduction in the molecular Weight ofsaid interpolymer, With from about 1% to about by Weight of maleicanhydride References Cited by the Examiner W. H. CANNON, AssistantExaminer.

6. A LUBRICATING COMPOSITION COMPRISING A MAJOR PROPORTION OF ALUBRICATING OIL AND A MINOR PROPORTION, SUFFICIENT TO IMPARTSLUDGE-INHIBITING AND DETERGENT PROPERTIES THERETO, OF ANITROGEN-CONTAINING COMPOSITION PREPARED BY THE PROCESS COMPRISINGREACTING AN OXIDIZED, DEGRADED INTERPOLYMER OF PROPYLENE AND ETHYLENE,SAID OXIDIZED, DEGRADED INTERPOLYMER HAVING A MOLECULAR WEIGHT OF ATLEAST ABOUT 1000 AND BEING OBTAINED BY HEATING SAID INTERPOLYMER AT ATEMPERATURE OF AT LEAST ABOUT 100*C. IN THE PRESENCE OF OXYGEN TO CAUSEA SUBSTANTIAL REDUCTION IN THE MOLECULAR WEIGHT OF SAID INTERPOLYMER,WITH FROM ABOUT 1% TO ABOUT 20% BY WEIGHT OF MALEIC ANHYDRIDE TO FROM ANACIDIC INTERMEDIATE AND NEUTRALIZING SAID ACIDIC INTERMEDIATE WITH ANALKYLENE POLYAMINE.